Title:
METAL-ORGANIC FRAMEWORK HAVING TEREPHTHALIC ACID BASED LIGAND
Document Type and Number:
WIPO Patent Application WO/2020/262451
Kind Code:
A1
Abstract:
The invention addresses the problem that metal-organic frameworks have conventionally only been produced with terephthalic acids having a limited range of substituents even though the amount and type of gas stored thereby can vary depending on the type of substituents. The objective of the present invention is to provide a novel metal-organic framework using a 2,5-disubstituted terephthalic acid. The metal-organic framework obtained through the binding of a carboxylic acid ion represented by formula (I) with a polyvalent metal ion, is a novel metal-organic framework and is capable of storing gases such as hydrogen and nitrogen efficiently. (In formula (I), X represents an unsubstituted or a substituted cycloalkyl group, an unsubstituted or a substituted aryl group, an unsubstituted or a substituted heterocyclyl group, or -Si(R1)(R2)(R3), and Y represents a single bond, an alkylene group, -O-, -S-, -S(O)-, -SO2-, or -N(R4)-, or a group combining these, with the proviso that phenyl groups, benzyloxy groups, pyrazole-1-yl groups, and groups represented by formula (II) when m equals 3, 6, 8, 9, 10, 11 and 12, are excluded as X-Y-.)
Inventors:
MINOURA MAO (JP)
SUGAMATA KOH (JP)
YANAGISAWA DAICHI (JP)
KOBAYASHI SHO (JP)
IIHAMA TERUYUKI (JP)
SUGAMATA KOH (JP)
YANAGISAWA DAICHI (JP)
KOBAYASHI SHO (JP)
IIHAMA TERUYUKI (JP)
Application Number:
PCT/JP2020/024770
Publication Date:
December 30, 2020
Filing Date:
June 24, 2020
Export Citation:
Assignee:
RIKKYO EDUCATIONAL CORP (JP)
NIPPON SODA CO (JP)
NIPPON SODA CO (JP)
International Classes:
C07C63/331; B01J20/22; C01B3/00; C07C63/49; C07C63/72; C07C65/24; C07C229/62; C07C323/62; C07D213/55; C07D213/68; C07D307/54; C07D333/24; C07F7/08; C07F1/08; C07F3/06; C07F7/00; C07F15/04
Foreign References:
| CN105713024A | 2016-06-29 | |||
| JP2008535657A | 2008-09-04 | |||
| JP2017512637A | 2017-05-25 | |||
| JP2017509607A | 2017-04-06 | |||
| JP2019117163A | 2019-07-18 | |||
| US20100075123A1 | 2010-03-25 |
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A. SCHNEEMANNE. D. BLOCHS. HENKEP. L. LLEWELLYNJ. R. LONGR. A. FISCHER, EUR. CHEM. J., vol. 21, 2015, pages 18764
E. GAOJ. XINGY. QUX, QIUM. ZHU, APPL. ORGANOMETAL CHEM., vol. 32, 2018, pages e4469
X. ZHENGS. Q. GUOX. Y. YUJ. K. HUY. H. LUOH. ZHANGX. CHEN, INORGANIC CHEMISTRY COMMUNICATION, vol. 18, 2012, pages 29
F. YUEB. LIX. ZHUY. LUOJ. HUX. WANGH. ZHANG, JOURNAL OF COORDINATION CHEMISTRY, vol. 66, no. 2, 2013, pages 243
H. DENGC. J. DOONAH. FURUKAWAR. B. FERREIRAJ. TOWNEC. B. KNOBLERB. WANG0. M. YAGHI, SCIENCE, vol. 327, 2010, pages 846
J. GASCONM. D. HERNANDEZ-ALONSONA. R. ALMEIDAG. P. M. VAN KLINKF. KAPTEIJING. MUI, CHEMSUSCHEM, vol. 1, 2008, pages 981
E. R. ENGELA. JOUAITIC. X. BEZUIDENHOUTM. W. HOSSEINIL. J. BARBOUR, ANGEW. CHEM. INT. ED., vol. 56, 2017, pages 8874
PAN, Y. ET AL.: "A new three-dimensional zinc-based metal-organic framework as a fluorescent sensor for detection of cadmium ion and nitrobenzene", JOURNAL OF COLLOID AND INTERFACE SCIENCE, vol. 513, 1 March 2018 (2018-03-01), pages 418 - 426, XP055781395
LI, L. ET AL.: "Ratiometric Luminescent Sensor of Picric Acid Based on the Dual-Emission Mixed-Lanthanide Coordination Polymer", ACS APPL. MATER. INTERFACES, vol. 10, no. 50, 21 November 2018 (2018-11-21), pages 44109 - 44115, XP055781396
YAN, W. ET AL.: "Two Lanthanide Metal-Organic Frameworks as Remarkably Selective and Sensitive Bifunctional Luminescence Sensor for Metal Ions and Small Organic Molecules", ACS APPL. MATER. INTERFACES, vol. 9, no. 2, 18 January 2017 (2017-01-18), pages 1629 - 1634, XP055781399
LU , L. ET AL.: "Systematic design and research on a series of cadmium coordination polymers assembled due to tetracarboxylate ligands", JOURNAL OF SOLID STATE CHEMISTRY, vol. 234, 2016, pages 93 - 102, XP029372527, DOI: 10.1016/j.jssc.2015.12.005
STASSEN, I. ET AL.: "Photopatterning of fluorescent host-guest carriers through pore activation of metal-organic framework single crystals", CHEM. COMMUN., vol. 53, no. 53, 7 July 2017 (2017-07-07), pages 7222 - 7225, XP055781400
ZHENG, X. ET AL.: "Two zinc(II) coordination polymers based on a benzenedicarboxylic acid derivative: Synthesis, crystal structures and luminescent properties", INORGANIC CHEMISTRY COMMUNICATIONS, vol. 18, 2012, pages 29 - 33, XP028464795, DOI: 10.1016/j.inoche.2012.01.001
PATEL, Y. S. ET AL.: "Studies on Novel Co-ordination Polymers Based on 2,5- bis(4-chlorophenylcarbamoyl)terephthalic acid and Divalent Transition Metal Ions", PELAGIA RESEARCH LIBRARY, vol. 2, no. 6, 2011, pages 58 - 67, XP055781402
CHOI, EUN-YOUNG ET AL.: "Layer-structured Metallopolymers with Pendant Carbazole Groups", BULL. KOREAN CHEM. SOC., vol. 33, no. 7, 20 July 2012 (2012-07-20), pages 2431 - 2434, XP055781403
CHOI, EUN-YOUNG ET AL.: "Single Crystals of a 2-Dimensional Metal Coordination Polymer Containing Pendant Carbazole Groups", BULL. KOREAN CHEM. SOC., vol. 34, no. 12, 20 December 2013 (2013-12-20), pages 3903 - 3905, XP055781405
GAO, E. ET AL.: "Synthesis, characterization, DNA binding, cytotoxicity and molecular docking properties of Cu (II) and Mn (II) complexes with 1,4-bis (pyrazol-1-yl) terephthalic acid", APPLIED ORGANOMETALLIC CHEMISTRY, vol. 32, no. 10, October 2018 (2018-10-01), pages e4469, XP055781406
SHO KOBAYASHI, ISAO SUGAMATA, TERUYUKI IIHAMA, MAO MINOURA: "2PB-059: Synthesis of metal-organic frameworks using silyl-substituted terephthalic acid and gas absorption capacity", PROCEEDINGS OF THE 100TH ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN; MARCH 22ND TO 25TH, 2020, vol. 100, 1 March 2020 (2020-03-01), JP, pages 2PB - 059, XP009532382
ISAO SUGAMATA, TERUYUKI IIHAMA, MAO MINOURA: "1 PA-104 Evaluation of gas adsorption characteristics of metal-organic frameworks using terephthalic acid derivatives", PROCEEDINGS OF THE 100TH ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN; MARCH 22ND TO 25TH, 2020, vol. 100, 1 March 2020 (2020-03-01), JP, pages 1 PA-104, XP009532383
ISAO SUGAMATA : "P-20: Synthesis and gas adsorption characteristics of metal-organic frameworks using 2,5-dialkylterephthalic acid as a ligand", PROCEEDINGS OF THE 33RD JAPAN SOCIETY ON ADSORPTION RESEARCH PRESENTATION; NOVEMBER 14 - 15, 2019, vol. 33, 14 November 2019 (2019-11-14), pages 72, XP009532388
H. LIM. EDDAUDIM. O'KEEFE0. M. YAGHI, NATURE, vol. 402, 1999, pages 276
M. EDDAUDIJ. KIMN. ROSID. VODAKJ. WACHTERM. O'KEEFE0. M. YAGHI, SCIENCE, vol. 295, no. 5554, 2002, pages 469
S. KAYEA. DAILY0. M. YAGHIJ. LONG, J. AM. CHEM. SOC., vol. 129, no. 46, 2007, pages 14176
E. Y. CHOIS. H. LEE0. P. KWON, BULL. KOREAN CHEM. SOC., vol. 33, no. 7, 2012, pages 2431
E. Y. CHOIS. B. LEEH. YUNS. H. LEEC. GAOY. SHIN0. P. KWON, BULL. KOREAN CHEM. SOC., vol. 34, no. 12, 2013, pages 3903
E. Y. CHOIC. GAOH. J. LEE0. P. KWONS. H. LEE, CHEM. COMUNN., 2009, pages 7563
T. YAMADAH. KITAGAWA, SUPRAMOLECULAR CHEMISTRY, vol. 23, 2011, pages 315
A. SCHNEEMANNE. D. BLOCHS. HENKEP. L. LLEWELLYNJ. R. LONGR. A. FISCHER, EUR. CHEM. J., vol. 21, 2015, pages 18764
E. GAOJ. XINGY. QUX, QIUM. ZHU, APPL. ORGANOMETAL CHEM., vol. 32, 2018, pages e4469
X. ZHENGS. Q. GUOX. Y. YUJ. K. HUY. H. LUOH. ZHANGX. CHEN, INORGANIC CHEMISTRY COMMUNICATION, vol. 18, 2012, pages 29
F. YUEB. LIX. ZHUY. LUOJ. HUX. WANGH. ZHANG, JOURNAL OF COORDINATION CHEMISTRY, vol. 66, no. 2, 2013, pages 243
H. DENGC. J. DOONAH. FURUKAWAR. B. FERREIRAJ. TOWNEC. B. KNOBLERB. WANG0. M. YAGHI, SCIENCE, vol. 327, 2010, pages 846
J. GASCONM. D. HERNANDEZ-ALONSONA. R. ALMEIDAG. P. M. VAN KLINKF. KAPTEIJING. MUI, CHEMSUSCHEM, vol. 1, 2008, pages 981
E. R. ENGELA. JOUAITIC. X. BEZUIDENHOUTM. W. HOSSEINIL. J. BARBOUR, ANGEW. CHEM. INT. ED., vol. 56, 2017, pages 8874
Attorney, Agent or Firm:
HIROTA, Masanori (JP)
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